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5 Lepadiformine is a cytotoxic agent (toxic to cells)
Chapter 13, Problem 13.65(choose chapter or problem)
5 Lepadiformine is a cytotoxic agent (toxic to cells) isolated from a marine tunicate. During a recent synthesis of lepadiformine, the investigators observed the formation of an interesting byproduct (3) while treating diol 1 with a reagent similar in function to PBr3 (J. Org. Chem. 2012, 77, 33903400): OH R HO PBr3 O R 3 dibromide 1 2 + (a) Draw a structure for the desired product (2). (b) Propose a plausible mechanism for formation of byproduct 3 using PBr3 as the reagent. Make sure that your mechanism provides a justification for the stereochemical outcome.
Questions & Answers
QUESTION:
5 Lepadiformine is a cytotoxic agent (toxic to cells) isolated from a marine tunicate. During a recent synthesis of lepadiformine, the investigators observed the formation of an interesting byproduct (3) while treating diol 1 with a reagent similar in function to PBr3 (J. Org. Chem. 2012, 77, 33903400): OH R HO PBr3 O R 3 dibromide 1 2 + (a) Draw a structure for the desired product (2). (b) Propose a plausible mechanism for formation of byproduct 3 using PBr3 as the reagent. Make sure that your mechanism provides a justification for the stereochemical outcome.
ANSWER:Problem 13.65Lepadiformine is a cytotoxic agent (toxic to cells) isolated from a marine tunicate. During arecent synthesis of lepadiformine, the investigators observed the formation of an interestingbyproduct (3) while treating diol 1 with a reagent similar in function to PBr (J3 Org. Chem. 2012,77, 33903400):(a) Draw a structure for the desired product (2).(b) Propose a plausible mechanism for formation of byproduct 3 using PBr as the reagent3Make sure that your mechanism provides a justification for the stereochemical outcome. Step-by-step solution Step 1 of 2PBr3epadiformine is a cytotoxic agent (toxic to cells) isolated from a marine tunicate.The reaction between and an alcohol: -a)Alcohols convert to alkyl bromine,